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Literature DB >> 33957045

AoiQ Catalyzes Geminal Dichlorination of 1,3-Diketone Natural Products.

Mengting Liu¹, Masao Ohashi, Yiu-Sun Hung, Kirstin Scherlach², Kenji Watanabe³, Christian Hertweck^2,4, Yi Tang.

Abstract

Enzymes that can perform halogenation of aliphatic carbons are of significant interest to the synthetic and biocatalysis communities. Here we describe the characterization of AoiQ, a single-component flavin-dependent halogenase (FDH) that catalyzes gem-dichlorination of 1,3-diketone substrates in the biosynthesis of dichlorodiaporthin. AoiQ represents the first biochemically reconstituted FDH that can halogenate an enolizable sp3-hybridized carbon atom.

Entities: Chemical

Mesh：

Substances：

Year: 2021 PMID： 33957045 PMCID： PMC8434754 DOI： 10.1021/jacs.1c02868

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

29 in total

1. Overexpressing transcriptional regulator in Aspergillus oryzae activates a silent biosynthetic pathway to produce a novel polyketide.

Authors: Takehito Nakazawa; Kan'ichiro Ishiuchi; Alex Praseuth; Hiroshi Noguchi; Kinya Hotta; Kenji Watanabe
Journal: Chembiochem Date: 2012-03-23 Impact factor: 3.164

2. A family of radical halogenases for the engineering of amino-acid-based products.

Authors: Monica E Neugebauer; Kiera H Sumida; Jeffrey G Pelton; Jonathan L McMurry; Jorge A Marchand; Michelle C Y Chang
Journal: Nat Chem Biol Date: 2019-09-23 Impact factor: 15.040

3. Regioselective Dichlorination of a Non-Activated Aliphatic Carbon Atom and Phenolic Bismethylation by a Multifunctional Fungal Flavoenzyme.

Authors: Pranatchareeya Chankhamjon; Yuta Tsunematsu; Mie Ishida-Ito; Yuzuka Sasa; Florian Meyer; Daniela Boettger-Schmidt; Barbara Urbansky; Klaus-Dieter Menzel; Kirstin Scherlach; Kenji Watanabe; Christian Hertweck
Journal: Angew Chem Int Ed Engl Date: 2016-08-25 Impact factor: 15.336

4. Total Enzyme Syntheses of Napyradiomycins A1 and B1.

Authors: Shaun M K McKinnie; Zachary D Miles; Peter A Jordan; Takayoshi Awakawa; Henry P Pepper; Lauren A M Murray; Jonathan H George; Bradley S Moore
Journal: J Am Chem Soc Date: 2018-12-14 Impact factor: 15.419

5. Degradation pathway of homoserine lactone bacterial signal molecules by halogen antimicrobials identified by liquid chromatography with photodiode array and mass spectrometric detection.

Authors: J J Michels; E J Allain; S A Borchardt; P Hu; W F McCoy
Journal: J Chromatogr A Date: 2000-11-17 Impact factor: 4.759

AoiQ Catalyzes Geminal Dichlorination of 1,3-Diketone Natural Products.

1. Overexpressing transcriptional regulator in Aspergillus oryzae activates a silent biosynthetic pathway to produce a novel polyketide.

2. A family of radical halogenases for the engineering of amino-acid-based products.

3. Regioselective Dichlorination of a Non-Activated Aliphatic Carbon Atom and Phenolic Bismethylation by a Multifunctional Fungal Flavoenzyme.

4. Total Enzyme Syntheses of Napyradiomycins A1 and B1.

5. Degradation pathway of homoserine lactone bacterial signal molecules by halogen antimicrobials identified by liquid chromatography with photodiode array and mass spectrometric detection.

6. Chlorination by a long-lived intermediate in the mechanism of flavin-dependent halogenases.

7. Complete reconstitution of a highly reducing iterative polyketide synthase.

8. Modern Transition-Metal-Catalyzed Carbon-Halogen Bond Formation.

9. Tryptophan 7-halogenase (PrnA) structure suggests a mechanism for regioselective chlorination.

10. Biosynthesis of polybrominated aromatic organic compounds by marine bacteria.

1. Heterologous Expression of Secondary Metabolite Genes in Trichoderma reesei for Waste Valorization.